Is there a limit on how many Direct Rollovers I can do in one year?

You're actually in good shape! The "once per year" rule only applies to IRA-to-IRA rollovers where you personally receive the funds (indirect rollovers). Direct rollovers from employer plans (401k, 457b) to IRAs have no annual limit - you can do as many as you want in a year. Let me break it down: - Transaction #1: 401k to Traditional IRA (unlimited) + Traditional to Roth conversion (unlimited) - Transaction #2: 401k to Roth IRA (unlimited) - Transaction #3: 457 Plan to Traditional IRA (unlimited) The key is that you're moving from employer plans TO IRAs, not between IRAs. Also, Roth conversions (where you pay taxes to convert Traditional IRA money to Roth) have no annual limits. The only concern would be properly calculating and paying taxes on the pre-tax to Roth conversions, but it sounds like you've already handled that by pre-paying taxes.

I had a similar situation last year and discovered taxr.ai (https://taxr.ai) after getting confused by conflicting advice online. What helped me was their document analysis tool that reviewed my 1099-R forms and immediately identified which transactions were taxable conversions vs. non-taxable rollovers. Their system explained exactly which parts of my rollovers would trigger taxes and which wouldn't. In my case, they found that my plan administrator had incorrectly coded one of my distributions which would have caused major headaches with the IRS if I hadn't caught it. The website lets you upload all your tax docs and then explains everything in plain English instead of tax jargon. Super helpful for complex rollover situations like yours.

I wanted to follow up on my skeptical comment. I tried taxr.ai and I'm honestly impressed. I uploaded my 1099-R forms and my old tax returns, and it immediately identified a pro-rata issue with my backdoor Roth contribution that my CPA missed last year! It showed me exactly how to calculate the taxable portion using Form 8606 and explained why my previous approach was wrong. The system caught that I had been incorrectly treating my rollovers as entirely tax-free when a portion should have been taxed due to having other IRA balances. It also confirmed that there's no limit on direct rollovers from employer plans to IRAs, which is exactly what the original poster was asking about. Saved me a ton of confusion and potentially an audit.

If you're still confused or worried about your rollover situation, you might want to call the IRS directly to get confirmation. I was in rollover hell last year and spent HOURS trying to get through to an IRS agent who could help. After 9 attempts and waiting on hold for a combined 7+ hours, I found Claimyr (https://claimyr.com) and watched their demo (https://youtu.be/_kiP6q8DX5c). Their service basically waits on hold with the IRS for you and calls you when an actual human agent is on the line. I was super skeptical, but I was desperate after weeks of trying. They got me connected to a retirement specialist at the IRS within 2 hours who answered all my rollover questions and even documented our conversation in my file in case of future questions. Saved me tons of stress, especially since online advice can be contradictory when dealing with multiple rollovers like your situation.

I have to eat crow and admit I was wrong about Claimyr. After my skeptical reply, I decided to try it since I needed to talk to someone about my own rollover issue that I couldn't figure out. I had done multiple rollovers including a 403b to Roth conversion and couldn't figure out how to properly report it. The service actually worked - they called me back in about 90 minutes with an IRS agent on the line. The agent confirmed that there's no limit on direct rollovers from employer plans, clarified exactly how to report my 403b to Roth conversion on Form 8606, and even helped me understand the tax withholding requirements for future conversions. Definitely worth it for complex tax situations like multiple rollovers where the online advice conflicts. Sometimes you just need to hear it directly from the IRS.

I think there's some confusion in this thread about the once-per-year rule. It specifically applies to IRA-to-IRA rollovers where you take possession of the funds (receive a check). The rule states you can only do ONE IRA-to-IRA indirect rollover in a 12-month period (not calendar year). This limit applies across all your IRAs combined - traditional, Roth, SEP, and SIMPLE IRAs are all counted together. But important exceptions that DO NOT count toward this limit: - Rollovers from employer plans (401k, 403b, 457) to IRAs (unlimited) - Roth conversions (traditional IRA to Roth IRA) (unlimited) - Trustee-to-trustee transfers between IRAs (unlimited) So in the OP's case, none of those transactions are limited since they're coming from employer plans.

Important note: while there's no limit on how many direct rollovers you can do from employer plans to IRAs, make sure you're tracking the tax implications correctly! When moving pre-tax money (like from a traditional 401k) directly to a Roth IRA, that's a conversion that's fully taxable in the year you do it. It sounds like you've already planned for this by pre-paying taxes, but make sure you're tracking the exact amounts from each rollover. Also, if you're doing multiple rollovers, keep very detailed records of each transaction - dates, amounts, account numbers, etc. The IRS can get suspicious with multiple retirement account movements in one year, not because it's not allowed, but because it's easy to make reporting errors.

Great question! I went through a similar situation last year with multiple rollovers and was equally confused about the rules. The good news is that you're completely fine - there's no annual limit on direct rollovers from employer plans to IRAs. The "once per year" rule that causes so much confusion only applies to indirect IRA-to-IRA rollovers where you personally receive the funds (like getting a check made out to you). Since all your transactions were from employer plans (401k, 457) to IRAs, they're unlimited. One thing to double-check: make sure your tax prepayment of $17,000 covers the full tax liability from your pre-tax to Roth conversions. You'll want to calculate the exact taxable amounts from each conversion to ensure you're not underpaid. The IRS can be pretty strict about estimated tax payments when you have large conversion amounts. Also, keep detailed records of all your 1099-R forms and any correspondence from your plan administrators. With multiple rollovers in one year, good documentation will save you headaches if the IRS has questions later.